Cookies And Cream Cinnamon Rolls

Southern Living Cookies and Cream Cinnamon Rolls in the skillet ready to serve
PHOTO: FRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY

Active Time:

50 mins

Rise Time:

2 hrs 30 mins

Total Time:

4 hrs 25 mins

Servings:

12

Just when you thought cinnamon rolls couldn’t get better, we added chocolate cookies and a creamy icing to make these incredibly gooey and rich cookies and cream cinnamon rolls. The interior of the cinnamon rolls is light and tender, and the bottoms are a little crispy and glazed from the filling. There’s chocolate in the filling, cookies in the icing, and loads of flavor from top to bottom.

We opted not to include crushed cookies in the filling or dough because they soften after a long proof and bake and end up with a texture we did not love. Instead, we added cocoa powder and cinnamon to the filling to complement the chocolate in the icing. And the icing—oh, the icing! It really delivers the cookies and cream flavor profile.

Learn how to make cookies and cream cinnamon rolls, and serve these up for a special breakfast, birthday brunch, or holiday dessert.

Ingredients for Cookies and Cream Cinnamon Rolls

Give homemade cinnamon rolls a cookies-and-cream makeover. Here are the ingredients you’ll need.

  • For the Dough: Bread milk is the flour we like, as it lends these rolls a much fluffier crumb once baked. You’ll want to use instant or quick-rising yeast to get these rolls moving along in the two rounds of proofing. Milk, granulated sugar, butter, vanilla extract, and kosher salt finish out the dough.
  • For the Filling: A classic filling uses sugar, cinnamon, and a pinch of kosher salt. But for the cookie flavor, we’re adding unsweetened cocoa. It’s all spread on a layer of softened unsalted butter.
  • For the Icing: Cream cheese is the base of the icing, and it melts beautifully when spread over the hot rolls. It’s mixed with butter, powdered sugar, salt, vanilla extract, and a hefty dose of cream-filled chocolate sandwich cookies. A final sprinkle of cookies finishes off these rolls.
Southern Living Cookies and Cream Cinnamon Rolls ingredients
FRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY

How To Make Cookies and Cream Cinnamon Rolls

As with all yeasted cinnamon rolls, you’ll need time for these to rise (twice). But besides that, this is a fairly straightforward recipe. Here’s a brief outline; the full recipe is further below.

  • Make the dough: We use the Tangzhong (a type of milk bread) method for these rolls: You cook a percentage of the flour and liquid in your recipe until the consistency resembles pudding. The liquid gelatinizes the starches, which can hold onto water better, producing softer rolls. Bread flour is traditionally used in this method, so that’s what we called for.
  • Make the filling: While the dough is rising the first time, make the filling and set it aside.
  • Roll out the dough: Once the dough has risen, it’s time to roll out and assemble the rolls. Once you’ve made a rectangle of dough, spread the butter, and sprinkle on the filling. Then roll the dough, and cut into individual rolls. We suggest a sharp knife so you can more cleanly cut the soft dough.
  • Second rise: Move the individual rolls to a buttered cast-iron skillet, and let them rise again.
  • Bake: Bake until the rolls are cooked through. Remove, and let cool 20 minutes.
  • Make the icing: While the rolls cool slightly, make the icing.
  • Spread the icing: Finish the rolls by spreading the icing over the warm rolls. Sprinkle with remaining cookies, and serve.

Tips for the Best Cinnamon Rolls

If you’re not an experienced cinnamon roll maker, you don’t have to worry. We’ve got some great tips for making them even better and easier. And, once you make your first batch, you’ll feel confident to make these all the time.

  • Use a bench knife, a sharp chef’s knife, or a serrated knife to cut the cinnamon rolls so you don’t smash them and can keep that vibrant spiral.
  • Aim for a rectangle rather than an oval when rolling out the dough for pretty and evenly shaped cinnamon rolls.
  • Leaving a bit more space in the center of the cast-iron skillet (and not overloading it with rolls) helps with the overall bake of the whole skillet, as the ones on the edge will bake much faster than the center rolls.

How To Store Cookies and Cream Cinnamon Rolls

Store leftover cinnamon rolls in an airtight container in the fridge for up to 3 days. Reheat in 10-second intervals in the microwave if you want the rolls warm again before enjoying.

A genius tip from the Test Kitchen: Place cinnamon rolls, icing side up, on the lid of an airtight container. Then, place the container on top of the cinnamon rolls so the icing won’t be squished.

How To Freeze Cookies and Cream Cinnamon Rolls

Freeze baked, uniced cinnamon rolls individually, and thaw them in the microwave until warm.

You can also freeze all of the baked cinnamon rolls together, once cool. Wrap them in plastic wrap, then aluminum foil, and store in an ziplock bag or airtight container up to 3 months in the freezer. Thaw overnight in the fridge, and warm in the oven. While the rolls are warming, make the icing, and spread it on the rolls just before serving.

Substitutions and Variations

If you want to change a few things up, consider these ideas from the Test Kitchen:

  • Substitute the classic cream-filled chocolate Oreos for Golden Oreos or any sandwich cookies you like.
  • Add some cocoa powder to the dough for a darker color.
  • Use black cocoa powder instead of regular cocoa powder in the filling. Black cocoa powder has a deeper chocolate flavor, closer to the classic Oreo flavor.

More Breakfast Breads

If you love these cinnamon rolls, try one of these favorites next:

  • Ambrosia Cinnamon Rolls
  • Christmas Morning Cinnamon Rolls
  • Cinnamon Rolls With Cream Cheese Frosting
  • Red Velvet Cinnamon Rolls
  • Caramel Rolls

Ingredients

Dough:

  • 1 1/3 cups, plus 1/3 cup whole milk, divided
  • 4 cups (about 17 oz.) bread flour, divided, plus more for work surface
  • 1/2 cup granulated sugar
  • 6 Tbsp. (3 oz.) unsalted butter, cut into pieces and softened, plus more for greasing
  • 1 3/4 tsp. instant or quick-rising yeast (such as Fleischmann’s RapidRise)
  • 1 1/2 tsp. vanilla extract
  • 1 tsp. kosher salt

Filling:

  • 1/3 cup (2 2/3 oz.) unsalted butter, melted
  • 1 cup granulated sugar
  • 3 Tbsp. unsweetened cocoa
  • 1/4 tsp. ground cinnamon
  • Pinch of kosher salt

Cookies and Cream Icing:

  • 4 oz. cream cheese, softened
  • 3 Tbsp. unsalted butter, softened
  • 1 cup (4 oz.) unsifted powdered sugar
  • 1 Tbsp. whole milk
  • 1 tsp. vanilla extract
  • 1 cup coarsely crushed cream-filled chocolate sandwich cookies (about 10 cookies) (such as Oreos), divided

Directions

  1. Prepare the Dough:Heat 1/3 cup of the milk and 2 tablespoons of the flour in a small saucepan over medium, whisking constantly, until thickened and whisk leaves lines of the milk mixture on bottom of pan, 1 minute, 30 seconds to 2 minutes. Scrape milk mixture into bowl of stand mixer fitted with a dough hook attachment.Southern Living Cookies and Cream Cinnamon Rolls milk mixture in saucepanFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  2. Add sugar, butter, yeast, vanilla, salt, and remaining 1 1/3 cups milk, and whisk until combined. (Mixture may be lumpy.)Southern Living Cookies and Cream Cinnamon Rolls adding the butter, yeast, and sugar FRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  3. Add remaining 3 3/4 cups plus 2 tablespoons flour. Beat on low speed until combined and no spots of dry flour remain, about 30 seconds, stopping to scrape down sides as needed. Increase speed to medium-low, and beat until dough is smooth and elastic, about 18 to 20 minutes.Southern Living Cookies and Cream Cinnamon Rolls dough after mixingFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  4. Let Dough rise:Shape into a ball, and place in a large bowl lightly greased with butter. Cover with plastic wrap, and let rise in a warm place, free from drafts, until puffed but not doubled in volume, 1 hour, 30 minutes to 2 hours.Southern Living Cookies and Cream Cinnamon Rolls dough after risingFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  5. While Dough rises, prepare the Filling:Stir together butter, granulated sugar, cocoa, cinnamon, and salt in a small bowl until thoroughly combined; set aside.Southern Living Cookies and Cream Cinnamon Rolls stirring together the fillingFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  6. Assemble rolls:Punch Dough down, and place on a lightly floured work surface. Roll Dough into an 18- x 14-inch rectangle. Evenly spread Filling over Dough using back of a spoon or a small offset spatula.Southern Living Cookies and Cream Cinnamon Rolls spreading the filling over the doughFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  7. Starting with 1 long side, roll up Dough, jelly roll style, gently pressing ends to maintain an 18-inch length. Place log seam side down. Using a serrated knife, cut into 12 (1 1/2-inch-thick) rolls.Southern Living Cookies and Cream Cinnamon Rolls forming the dough into a logFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  8. Add rolls to skillet:Place rolls, cut sides down, in a (12-inch) cast-iron skillet greased with butter, spaced evenly apart with 9 rolls around edge of skillet and 3 rolls in center. Cover with plastic wrap.Southern Living Cookies and Cream Cinnamon Rolls in the pan before risingFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  9. Let rolls rise:Let rolls rise in a warm place, free from drafts, until doubled in volume, about 1 hour to 1 hour, 30 minutes.Southern Living Cookies and Cream Cinnamon Rolls FRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  10. Bake rolls:Preheat oven to 350°F. Bake rolls in preheated oven until golden brown and a thermometer inserted into thickest portion of center of rolls registers 180°F, about 30 to 35 minutes, tenting with aluminum foil after 25 minutes cook time. Let cool in skillet on a wire rack 20 minutes.Southern Living Cookies and Cream Cinnamon Rolls in the skillet after bakingFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  11. While rolls cool, prepare the Cookies And Cream Icing:Beat cream cheese and butter with an electric mixer on medium speed until creamy, about 20 seconds. Gradually add powdered sugar, beating at low speed until creamy and smooth, about 1 minute. Stir in milk and vanilla until creamy; stir in 1/2 cup of the cookies.Southern Living Cookies and Cream Cinnamon Rolls preparing the toppingFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY
  12. Add Icing:Spread Cookies and Cream Icing over rolls.Southern Living Cookies and Cream Cinnamon Rolls spreading the frosting over the cinnamon rolls FRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEYTop with remaining 1/2 cup cookies. Serve warm.Southern Living Cookies and Cream Cinnamon Rolls on the plate ready to eatFRED HARDY, FOOD STYLIST: EMILY NABORS HALL, PROP STYLIST: CHRISTINA DALEY